Isolation and structural elucidation of new cyclotetrapeptides, trapoxins A and B, having detransformation activities as antitumor agents.
New cyclotetrapeptides, trapoxins A and B were isolated from the culture broth of Helicoma ambiens RF-1023. These compounds exhibit detransformation activities against v-sis oncogene-transformed NIH3T3 cells (sis/NIH3T3) as antitumor agents. The structures were found to be new cyclotetrapeptides, cyclo[(S)-phenylalanyl-(S)-phenylalanyl-(R)-pipecolinyl- (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoyl-] for trapoxin A and cyclo[(S)-phenylalanyl-(S)-phenylalanyl-(R)-prolyl-2- amino-8-oxo-9,10-epoxydecanoyl-] for trapoxin B, by X-ray analysis, mass spectrometric, NMR and chemical studies.
Itazaki
H
H
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
Nagashima
K
K
Sugita
K
K
Yoshida
H
H
Kawamura
Y
Y
Yasuda
Y
Y
Matsumoto
K
K
Ishii
K
K
Uotani
N
N
Nakai
H
H
D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002461:Cell Line, Transformed; D002471:Cell Transformation, Neoplastic / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D005285:Fermentation; D036341:Intercellular Signaling Peptides and Proteins; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D003904:Mitosporic Fungi / Q000378:metabolism*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010446:Peptide Fragments / Q000737:chemistry; D010455:Peptides; D010456:Peptides, Cyclic / Q000737:chemistry; D011487:Protein Conformation; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014961:X-Ray Diffraction
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D036341:Intercellular Signaling Peptides and Proteins; D010446:Peptide Fragments; D010455:Peptides; D010456:Peptides, Cyclic; C067070:trapoxin A; C067071:trapoxin B